What would you do?

Worth noting there's a fairly important distinction to be made between a roller furling and roller reefing.
 
For the relatively recently acquired family boat we have a furler, which is the first time I have ever owned such a thing having raced for 30+ years.

The previous owner specced a smaller headsail with less overlap as his wife was having trouble winching in the big genny.

This actually suits me a treat as I never have to reef the jib in normal coastal sailing.

Depending on how your boat is rigged and canvassed it might be worth thinking about. Ours has a fractional rig with a big mainsail so I never need to do much past one or two reefs in the main.
You would be well advised to check your forestay for damage at the top of the foil, as it should not be necessary to use a winch to furl your headsail.
 
+1 for the above.

Check your halyard tension is not too tight. Some systems need the tension reduced a bit so they turn more easily.

And a yearly bearing check and lubricate helps.
 
You would be well advised to check your forestay for damage at the top of the foil, as it should not be necessary to use a winch to furl your headsail.
Think there may be some wires crossed here. The boat has a furling headsail which does not require any winching to furl. That furling headsail is smaller than the max size #1 genoa for the boat, because the big genoa was too large for the previous owners wife to tack. Apologies if that was not clear.
 
I used to have a furler (for over 15 years) but when I rerigged 2 years ago, I dumped the furler and went back to hanked on headsails. I didn’t like the shape of the partially furled sail, the extra weight and windage, the laziness it induced in me and its occasional jamming at the wrong moment.
 
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